Massachusetts Island Town #1 Most Expensive in America

Massachusetts island town named #1 most expensive in U.S.

Nestled on the idyllic island of Martha’s Vineyard, Vineyard Haven might look like a quaint coastal haven, but don’t let its charming facade fool you—it’s got a hefty price tag.

In fact, it recently snagged the title of the most expensive place to live in the entire United States, according to a study by LendingTree.

But rewind a few decades, and Vineyard Haven wasn’t always a playground for the rich and famous.

Martha’s Vineyard was a humble fishing community, its shores dotted with wooden boats and bustling docks. Back then, life was simple, and so were the property prices.

But as time ticked on and word of Martha’s Vineyard’s beauty spread like wildfire, tourists began to flock to its shores. What was once a quiet fishing village soon transformed into a hotspot for vacationers seeking sun, sand, and sea.

Thanks "Jaws!"

As the demand for Martha’s Vineyard and real estate soared, so did the prices. What used to be affordable beachfront cottages became million-dollar mansions seemingly overnight.

Vineyard Haven, in particular, felt the brunt of this real estate boom, with property values skyrocketing to unprecedented heights.

Nowadays, this Massachusetts island town is a playground for the elite—a place where billionaires rub elbows and beachfront estates are a dime a dozen. But beneath the glitz and glamour lies a rich history steeped in maritime tradition and small-town charm.

Despite its astronomical real estate prices, Vineyard Haven still retains traces of its quaint past.

Stroll along its cobblestone streets, and you’ll find historic homes dating back centuries, each with its own story to tell. Duck into Waterside Market  and you’ll be greeted by friendly faces and the aroma of freshly brewed coffee.

But make no mistake—living in this Massachusetts island town comes with a hefty price tag. From multi-million dollar estates overlooking the ocean to cozy cottages tucked away in the woods, every square inch of this picturesque town comes at a premium.

And while some may bemoan the loss of Vineyard Haven’s humble roots, others see it as a sign of progress—a testament to Martha’s Vineyard’s enduring allure. A

fter all, where else can you find such natural beauty, rich history, and unabashed luxury all in one place?

Not to mention the Obamas, Larry David, Amy Schumer and Ted Danson? (That's just a smattering of celebs!0

So, while Vineyard Haven may be the most expensive place to live in the United States, its allure remains as strong as ever. And for those lucky enough to call it home, the price tag is just a small price to pay for paradise.

Martha's Vineyard is a haven of natural beauty, rich history, and quintessential New England charm. It also happens to be the place where I got engaged to my husband, Rob, and where we went on our "babymoon!" With its pristine beaches, picturesque landscapes, and vibrant communities, Martha's Vineyard attracts visitors seeking an exclusive, fancy escape.

Martha's Vineyard has it all! The sandy beaches, the bougie restaurants, the raw bars along the water, the enormous houses, and quaint villages. No matter where you travel on the island, each little village looks like a perfect postcard scene.

I'll never forget when I saw the iconic gingerbread cottages in Oak Bluffs. And the serene shores of Aquinnah where I took my babymoon pregnancy photos. And you haven't lived unless you've gotten an ice cream in the bustling streets of Edgartown and passed along the "Jaws Bridge." Don't even get me started on the food! *chef's kiss*

For those seeking an intimate and charming experience, Martha's Vineyard is home to several exquisite bed and breakfasts. I used Tripadvisor to find the 5 most top-rated bed and breakfast's on the island. These are places that had great views, great reviews, and great service.

But don't forget, Martha's Vineyard is more than just charming accommodations. Visitors can explore the island's rich maritime history at the Martha's Vineyard Museum (which I have done!) They can take a stroll through the colorful streets of Vineyard Haven, or relax on the sandy shores of South Beach.

A word of advice to those traveling to Martha's Vineyard for the first time: rent a car. Unless you plan on staying in one place the entire time you're there, you'll want to use a car to get around and see all of the stunning places the Vineyard has to offer.

The Nobnocket Boutique Inn is the #1 rated bed and breakfast on Martha's Vineyard. According to Tripadvisor, the guests were incredibly impressed with the quality of the breakfast in the morning. They also liked that it wasn't in a busy MV area. Out of the 208 reviews, 207 of them rated this place "excellent."

https://www.nobnocket.com/

Nestled in Edgartown, The Charlotte Inn is a historic property known for its timeless elegance. Antique furnishings, manicured gardens, and impeccable service make it a favorite among discerning travelers.

https://www.thecharlotteinn.com/rooms-suites/

Located in the heart of Edgartown, The Hob Knob is a boutique bed and breakfast with a contemporary twist. Thoughtful details, personalized service, and a delightful ambiance set it apart. This is where my husband and I stayed on our babymoon. We loved that they were dog friendly and they had bicycles to rent from the hotel. We rode the bikes down to the Jaws Bridge! We're not the only ones who loved our experience, because The Hob Knob was also rated one of the top B&B's in Martha's Vineyard!

https://www.hobknob.com/

In the heart of Oak Bluffs, this inn exudes Victorian charm. With cozy rooms and a warm atmosphere, it's a delightful retreat after a day of exploring the island.

https://oakbluffsinn.com/

Tucked away in West Tisbury, Lambert's Cove Inn offers a tranquil escape surrounded by nature. With spacious grounds and an emphasis on relaxation, it's a perfect choice for those seeking serenity.

https://lambertscoveinn.com/